Walk-Off Wagers: MLB Best Bets Today (Predictions for Brewers-Cubs, Orioles-Rays, Bryan Woo)

Monday’s Major League Baseball action features 14 games, giving bettors a fun way to start the week.

There are a ton of pitching matchups that I’m interested in betting on tonight, but I’ve narrowed things down to just three plays, including a player prop for Seattle Mariners All-Star Bryan Woo, who has really come on in the month of May.

Plus, there are two home teams with star lefties on the mound that I believe are worth a look in their series openers.

Betting on Major League Baseball is super exciting since there are hundreds of markets to dive into. I’ve got a little something for everyone on May 18, including a player prop, a First 5 Innings bet and an outright moneyline to kick off the week!

MLB Best Bets for Monday, May 18

Odds via DraftKings Sportsbook

Tampa Bay Rays First 5 Innings Moneyline (-154) vs. Baltimore Orioles
Chicago Cubs Moneyline (-167) vs. Milwaukee Brewers
Bryan Woo 6+ Strikeouts (-176)

Tampa Bay Rays First 5 Innings Moneyline (-154) vs. Baltimore Orioles

The Tampa Bay Rays are in first place in the AL East, and they’ve been elite at home in the 2026 season, winning 16 of their 21 games.

So, I’m eyeing them as home favorites on Monday night against the Baltimore Orioles, who sit 10 games behind them in the standings. Baltimore is five games under .500, and it may have the lesser of the two starters on the mound on Monday.

Trevor Rogers (5.77 ERA) has not found the same form he had in 2025 when he posted a sub-2.00 ERA in 18 starts, and the O’s are just 3-4 in his seven starts in 2026. Rogers has allowed at least three runs in four straight starts, ranking in the 45th percentile in expected ERA this season.

Meanwhile, Rays All-Star Shane McClanahan has been lights out as of late, allowing just 11 hits and no runs over his last four starts. The Rays are now 6-2 when he’s on the mound, even though the lefty hasn’t worked deep into many ball games.

So, I’m eyeing Tampa in the first five innings when both of these starters should still be on the hill. McClanahan has a 2.27 ERA and an expected ERA in the 72nd percentile this season. Plus, Tampa Bay ranks third in MLB in batting average, 10th in OPS and 13th in runs scored.

The O’s are just 24th, 18th and 14th in those respective categories.

Chicago Cubs Moneyline (-167) vs. Milwaukee Brewers

Chicago Cubs lefty Shota Imanaga has been one of the best starters in MLB this season, posting a 2.32 ERA in nine starts.

Despite that, the Cubbies are just 4-5 when he’s on the mound. So, should bettors trust Chicago as a home favorite on Monday?

I think so, as the Milwaukee Brewers have a struggling righty in Brandon Sproat on the mound in this matchup. Sproat has a 5.75 ERA this season, and he ranks in the 26th percentile in expected ERA.

For comparison, Imanaga is in the 83rd percentile in expected ERA and the 80th percentile in expected batting average against.

The Cubs still have a lead over the Brewers in the division, and Milwaukee’s still ranks behind the Cubs’ attack in runs scored, OPS, batting average and Weighted Runs Created Plus (wRC+) this season.

On top of that, while home and road splits aren’t the only thing to look at when betting, Chicago is 18-5 at Wrigley Field while the Brewers – despite their recent 8-2 stretch – are just 11-9 on the road. I’ll take the Cubs to win this series opener with Imanaga on the bump.

Bryan Woo 6+ Strikeouts (-176)

The 2026 season has been a little up and down for Mariners right Bryan Woo, but he’s really pitched well in his last two outings.

After raising his ERA to 4.61 this season, Woo has knocked it back down to 3.91 by allowing just four hits and two runs over his last two outings.

He’s struck out nine batters in both of those starts, and the 26-year-old right-hander now has five outings with at least six strikeouts. So, I don’t mind backing him in this prop against the Chicago White Sox, who rank 26th in MLB in strikeouts per game (9.13).

Woo has at least nine punchouts in three outings, and while his strikeout percentage (49th percentile) is down, he’s cleared this line in three of his last five starts.

I’ll buy into Woo’s recent stretch of games, as the Mariners All-Star showed in 2025 that he can be a dominant rotation piece, posting a 2.94 ERA while striking out 9.5 batters per nine innings.

Odds refresh periodically and are subject to change.

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